Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations.

Enantioselective synthesis of bicyclo[3.n.1]alkanes by chiral phosphoric acid-catalyzed desymmetrizing Michael cyclizations† †Electronic supplementary information (ESI) available: Experimental procedures, spectroscopic data for new compounds, and crystallographic data for 2d, 3a, 6e, and 6f. CCDC 1045000–1045003. See DOI: 10.1039/c5sc00753d

Brønsted Acid Catalyzed Phosphoramidic Acid Additions to Alkenes: Diastereo- and Enantioselective Halogenative Cyclizations for the Synthesis of C- and P-Chiral Phosphoramidates

The first highly diastereo- and enantioselective additions of a halogen and phosphoramidic acid to unactivated alkenes have been developed, catalyzed by a chiral Brønsted acid. A unique feature of these additions is the opportunity for stereocontrol at two noncontiguous chiral centers, carbon and phosphorus, leading to cyclic P-chiral phosphoramidates. In addition to their inherent value, the p...

Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid.

We report a highly diastereo- and enantioselective synthesis of anti homoallylic alcohols from terminal alkynes via (E)-1-alkenylboronates based upon two catalytic reactions: a cationic iridium complex-catalyzed olefin transposition of (E)-1-alkenylboronates and a chiral phosphoric acid-catalyzed allylation reaction of aldehydes.

Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives

The importance and increased demand of pharmaceutically active azaheterocycles has urged the development of inexpensive and environmentally benign catalytic asymmetric technologies. 2] In this context, the pyrazolidine and pyrazoline structural motif is present in several compounds with significant bioactivities, such as anti-inflammatory, antidepressant, anticancer, antibacterial and antiviral...

Chiral phosphoric acid catalyzed enantioselective 1,3-dipolar cycloaddition reaction of azlactones.

The first chiral phosphoric acid catalyzed highly diastereo- and enantioselective 1,3-dipolar cycloaddition reaction of azlactones and methyleneindolinones was disclosed. By using a BINOL-derived chiral phosphoric acid as the catalyst, azlactones were activated as chiral anti N-protonated 1,3-dipoles to react with methyleneindolinones to yield biologically important 3,3'-pyrrolidonyl spirooxind...